Hydroxyphenylacetic acid → Ethyl 4-hydroxyphenylacetate

HRID 1900639Notes

Reaction equation

HRID 1900639 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[CH2:12](O)[CH3:13].O=S(Cl)Cl>C(OCC)(=O)C>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 127Hydroxyphenylacetic acidHCID 702EthanolHCID 24386Thionyl Chloride

Product 1

HCID 28310Ethyl 4-hydroxyphenylacetate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-hydroxyphenylacetic acid (g.12 g, 0.06 mol), absolute ethanol (50 mL) and SOCl2 (2 mL, 0.028 mol) was refluxed for 3 hours. The residue was cooled, diluted with ethyl acetate (200 L), washed first with dilute aqueous sodium bicarbonate (100 mL) and then twice with water (100 mL), then was dried over anhydrous MgSO4, filtered and evaporated in vacuo. Ethyl 4-hydroxyphenylacetate was obtained as an oil.

Workup

  1. temperaturewas refluxed for 3 hours
  2. temperatureThe residue was cooled
  3. washwashed first with dilute aqueous sodium bicarbonate (100 mL)
  4. dry with materialtwice with water (100 mL), then was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-32afa0bbe2e2410090aaced3422944b4
Source dataset
uspto-grants-1996_11
Patent number
US05576332

Reaction notes

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